N-bromobutanimide → Methyl 2-[2-(bromomethyl)phenyl]-2-oxoacetate

HRID 358910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 358910
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:13])[C:9]([O:11][CH3:12])=[O:10].[Br:14]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.[Hg]>[Br:14][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:13])[C:9]([O:11][CH3:12])=[O:10]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 3768392Methyl (2-methylphenyl)(oxo)acetate

Produkt 1

HCID 14697242Methyl 2-[2-(bromomethyl)phenyl]-2-oxoacetateAusbeute 49,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23931MercuryKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

5.34 g (30 millimoles) of methyl 2-methylphenylglyoxylate and 5.34 g (30 millimoles) of N-bromosuccinimide in 1,000 ml of tetrachloromethane are exposed to a 300 W mercury vapor lamp for one hour. Thereafter, the organic phase is washed once with water and three times with sodium bicarbonate solution, dried over sodium sulfate/sodium carbonate and evaporated down, and the crude product is then chromatographed over silica gel using 1:9 methyl tert-butyl ether/n-hexane. 3.8 g (49%) of the abovementioned compound are obtained as a yellow oil.

Aufarbeitung

  1. washThereafter, the organic phase is washed once with water and three times with sodium bicarbonate solution
  2. dry with materialdried over sodium sulfate/sodium carbonate
  3. customevaporated down
  4. customthe crude product is then chromatographed over silica gel using 1:9 methyl tert-butyl ether/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ff7a8885186b476cb1d39252b6e29ae4
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04997973

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